Category: Tetrahydropyrans

29943-42-8, Dihydro-2H-pyran-4(3H)-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a mixture of NaH(1.97 g, 44.96 mmol) in THF(100 ml) was added dropwise dihydro-2H-pyran-4(3H)-one(3 g, 29.96 mmol) in an ice bath. After stirring for 20 mi dimethyl carbonate(3.8 ml, 44.96 mmol) was added. The reaction mixture was stilTed at ft for 3 h. To a mixture of diethyl ether / iN HC1 was poured reaction mixture with stirring. The organic layer was separated, dried over Na2SO4, concentrated under reduced pressure and the residue was purified by column chromatography to afford the desired product 1-1(1.5 g) as a yellow liquid.1H NMR (300 MHz, CDC13) 5 11.752 (s, 1H), 4.267 (m, 2H), 3.863 (m, 2H), 3.783 (m, 2H), 3.758 (s, 3H), 2.393 (m, 2H), 1.85 1 (m, 2H).

29943-42-8, The synthetic route of 29943-42-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ST PHARM CO., LTD.; KIM, Kyungjin; KIM, Uk-Il; YOON, Ji Hye; (32 pag.)WO2017/99424; (2017); A1;,
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14774-37-9, Tetrahydropyran-4-methanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

TsCl (7.22 g, 37.9 mmol) was added portionwise to a solution of alcohol (9) (4.0 g, 34.44 mmol), Et3N(7.0 g, 69 mmol) and DMAP (0.05 g, 0.35 mmol) in dry DCM (50 mE) at 00 C. The reaction mixture was allowed to warm to room temperature and thrther stirred for 1 h. The reaction mixture was diluted with water, extracted with EtOAc, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give (tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate (10) as white solid. Yield (8.5 g, 91%); 1H NMR (400 MHz, DMSO-d5) delta 7.78 (d, J=8.0 Hz, 2H), 7.48 (d, J=8.0 Hz, 2H), 3.87 (d, J=6.4 Hz, 2H), 3.78 (dd, J=11.2, 4.2 Hz, 2H), 3.22 (dt, J=11.6, 1.6 Hz, 2H), 2.42 (s, 3H),1.88-1.79 (m, 1H), 1.46 (dd, J=12.8, 1.6 Hz, 2H), 1.18-1.07 (m, 2H).

14774-37-9, 14774-37-9 Tetrahydropyran-4-methanol 2773573, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; Acucela Inc.; Kuksa, Vladimir A.; Orme, Mark W.; Hong, Feng; Kubota, Ryo; US2014/275043; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

185815-59-2, 4-Isobutyldihydro-2H-pyran-2,6(3H)-dione is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 2 (i?)-3-(2-(Cinnamyloxy)-2-oxoethyl)-5-methylhexanoic acid, (III) Procedure AQuinine (28.7g, 88 mmol) was suspended in toluene (380 mL). Cinnamyl alcohol (15.5 g, 115 mmol) was added and the reaction mixture was cooled to -35 0C. The solution of 3- isobutylglutaric anhydride (15.0 g, 88 mmol) in toluene (10 mL) was added during 15 min and the reaction mixture was stirred at -35 C for 24 hours. Toluene solution was washed with 5% HCl (250 mL) and evaporated. Oily residue was dissolved in 2-PrOH (300 mL), warmed to 45 0C, and the solution of 1-adamantylamine (12.0 g, 79 mmol) in MTBE (100 mL) was added. The mixture was stirred at 25 0C for 6 hours, filtered, washed with 2-PrOH (100 mL) and dried under reduced pressure to yield 28.1 g of 1-adamantylamine salt of (/?)-3-(2-(cinnamyloxy)-2-oxoethyl)-5- methylhexanoic acid. The salt was suspended in toluene (15OmL) and stirred with 3% HCl (100 mL) until a clear solution was obtained. Aqueous acidic solution was separated and organic layer was washed once again with 3% HCl (3OmL). Evaporation of toluene afforded 18.1 g (69%) of monoester as viscous yellowish oil. HPLC analysis on Chiralpak AS column, hexane/EtOH/TFA=95/5/0.1 revealed 91.2 % ee. 1H NMR (CDCl3), delta/ppm: 0.87 (d, 6H, J=6.5 Hz), 1.21-1.27 (m, 2H), 1.56-1.70 (m, IH), 2.38-2.48 (m, 5H), 4.73 (dd, 2H, J/=6.5 Hz, J2=1.2 Hz), 6.27 (dt, IH J/=15.8 Hz, J2=6.5 Hz), 6.65 (d, IH, J=I 5.8 HZ), 7.22-7.40 (m, 2H).13C NMR (CDCl3), delta/ppm: 22.34, 25.07, 29.64, 38.30, 38.48, 43.26, 64.92, 122.95, 126.50, 127.96, 128.49, 134.18, 136.07, 172.26, 178.64., 185815-59-2

As the paragraph descriping shows that 185815-59-2 is playing an increasingly important role.

Reference£º
Patent; PLIVA ISTRAZIVANJE I RAZVOJ D.O.O.; MCLEISH, Nicholas, Alistair, Maxwell; WO2008/9897; (2008); A1;,
Tetrahydropyran – Wikipedia
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1152567-60-6, 4-(4-Bromophenyl)tetrahydro-2H-pyran-4-carboxylic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Method 52 Synthesis of 2-[4-(4-bromophenyl)tetrahydropyran-4-yl]-1H-benzimidazole (Intermediate 77) A mixture of I-51.2 (50 mg, 0.175 mmol), phenylenediamine (23 mg, 0.210 mmol), and triphenylphosphite (60 muL, 0.228 mmol) in pyridine (1 mL) is sealed in a vessel and heated at 150 C. for 18 h. After cooling to room temperature the reaction is diluted with DCM and washed with saturated aqueous NaHCO3. The organics are dried over anhydrous Na2SO4 and concentrated in vacuo. Purification is by flash chromatography (SiO2, DCM to 3% MeOH in DCM) to give the title intermediate I-79 (46 mg) m/z 357.0, 358.8 [M+H]., 1152567-60-6

As the paragraph descriping shows that 1152567-60-6 is playing an increasingly important role.

Reference£º
Patent; BARTOLOZZI, Alessandra; CHEN, Zhidong; DINES, Jonathon Alan; LO, Ho Yin; LOKE, Pui Leng; OLAGUE, Alan; RIETHER, Doris; TYE, Heather; WU, Lifen; ZINDELL, Renee M.; US2013/196967; (2013); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4677-18-3,2-(Tetrahydro-2H-pyran-4-yl)ethanol,as a common compound, the synthetic route is as follows.

To an ice-cold solution of 2-(tetrahydro-2H-pyran-4-yl)ethanol (1.00 g) in pyridine (6.5 mL) was added p-toluenesulfonyl chloride (1.5 g), followed by stirring at the same temperature for 30 minutes, and at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure, and then diluted aqueous hydrochloric acid (20 mL) was added to the residue, followed by twice extractions with ethyl acetate (20 mL). The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=80/20-50/50) to obtain p-toluenesulfonic acid 2-(tetrahydro-2H-pyran-4-yl)ethyl ester (450 mg)., 4677-18-3

The synthetic route of 4677-18-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Astellas Pharma Inc.; EP2194044; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

7525-64-6, 4-Methyltetrahydro-2H-pyran-4-ol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

7525-64-6, Step 1. Preparation of (4-methyltetrahydropyran-4-yl)-(4-nitrophenyl)-carbonate In a flame-dried round bottomed flask equipped with a magnetic stirrer, 4-methyltetrahydropyran-4-ol (1.5 g, 12.9 mmol), prepared as described in patent application WO2004/041161, was dissolved in CH2Cl2 (30 mL). The mixture was chilled to 0 C. then pyridine (2.04 mL, 25.82 mmol, 2 eq) and p-nitrophenylchloroformate (3.38 g, 16.78 mmol) solution in CH2Cl2 (10 mL) were slowly added. A white precipitate almost immediately appeared and the mixture was stirred overnight at rt. The crude mixture was then diluted with CH2Cl2, washed with 1M HCl solution, saturated NaHCO3 solution and finally with brine. The two phases were separated and the organic one was dried over Na2SO4. Removal of the organics under reduced pressure gave a crude yellow solid (3.8 g), as a 1:1 mixture of desired product and p-nitrophenylchloroformate, which was used in the next step without further purification. 1H NMR (CDCl3): delta 1.67 (s, 3H), 1.87 (m, 2H), 2.23 (m, 2H), 3.78 (m, 4H), 7.39 (d, J=9.0 Hz, 2H), 8.29 (d, J=9.0 Hz, 2H)

The synthetic route of 7525-64-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; The Regents of the University of California; Fondazione Istituto Italiano Di Technologia; Universita Degli Studi Di Parma; Universita Degli Studi Di Urbino ?Carlo Bo?; Piomelli, Daniele; Bandiera, Tiziano; Mor, Marco; Tarzia, Giorgio; Bertozzi, Fabio; Ponzano, Stefano; (102 pag.)US9353075; (2016); B2;,
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Tetrahydropyran – an overview | ScienceDirect Topics

101691-94-5, 4-(Iodomethyl)tetrahydro-2H-pyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2-(2,6-dichlorophenyl)-1 -[(1 S)-4-iodo-1-methyl-1 ,3-dihydro-2H-isoindol-2-yl]ethanone a48(100 mg, 0.22 mmol), sodium metabisulfite (87 mg, 0.45 mmol), tetrabutylammonium bromide (80 mg, 0.25 mmol), sodium formate (34 mg, 0.49 mmol), palladium(Il) acetate (5mg, 0.02 mmol), 1,10-phenanthroline (12 mg, 0.07 mmol) and triphenylphosphine (18 mg, 0.07 mmol) were mixed in DMSO (2 mL). The mixture was stirred at 70 C for 2 h. The reaction mixture was cooled to rt, then 4-(iodomethyl)tetrahydro-2H-pyran (100 mg, 0.44mmol) was added. The mixture was stirred at ft for 16 h, then diluted with DCM (50 mL) and successively washed with water (50 mL) and brine (50 mL). The organic layer was dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by reverse phase chromatography (basic mode, LCMS prep) to yield 12 mg of 2-(2,6- dichlorophenyl)-1 -{(1 S)-1 -methyl-4-[(tetrahydro-2H-pyran-4-ylmethyl)sulfonyl]- 1 ,3-dihydro-2H-isoindol-2-yl}ethanone 42 as a white solid.Yield: 10%.LCMS (ES) 482/484/486 (M-?-H), 96.78 % purity.

101691-94-5, As the paragraph descriping shows that 101691-94-5 is playing an increasingly important role.

Reference£º
Patent; UCB BIOPHARMA SPRL; SKOLC, David; ATES, Ali; JNOFF, Eric; VALADE, Anne; (99 pag.)WO2016/55482; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1768-64-5, 4-Chlorotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1768-64-5

9-Hydroxy-9-(tetrahydro-2H-pyran-4-yl)-9H-fluorene-2-carboxylic acid [FAB-MS: 309 (M – H)-] produced from 4-tetrahydro-2H-pyranyl magnesium chloride (prepared from 4-chlorotetrahydro-2H-pyran and magnesium) and 9-oxo-9H-fluorene-2-carboxylic acid in the same manner as in Reference Example 4-a was allowed to react with triethylsilane at room temperature in trifluoroacetic acid, thereby obtaining 9-(tetrahydro-2H-pyran-4-yl)-9H-fluorene-2-carboxylic acid. FAB-MS: 291 (M – H)-.

The synthetic route of 1768-64-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Astellas Pharma Inc.; EP1728784; (2006); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

14774-37-9, Tetrahydropyran-4-methanol is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,14774-37-9

Step 2: Synthesis of toluene-4-sulfonic acid tetrahydro-pyran-4-ylmethyl ester; Prepared as described by adaptation of the following literature reference:Radziszewski, J. G. et al. J. Am. Chem. Soc. 1993, 115, 8401.To a solution of 97 g (810 mmol) of (tetrahydro-pyran-4-yl)-methanol in 2-methyltetrahydrofuran (190 mL) are added 165 mL of 50% aqueous NaOH solution. To this stirred suspension is added dropwise with cooling a solution of p-toluene-sulfonylchloride (283 g, 1.46 mol) in 2-methyltetrahydrofuran (280 mL). The reaction is stirred at 30-35 C. for 18 h. The suspension is poured into a mixture of ice-water (280 mL) and aqueous HCl solution (37%, 203 mL). After addition of methylcyclohexane (1.4 L) and further ice-water (0.2 L), the reaction mixture is stirred for 2 h in an ice-bath. The resulting crystalline precipitate is isolated by filtration and washed with methylcyclohexane (0.5 L) and water (0.5 L). Drying under reduced pressure at 40 C. gave 216 g of toluene-4-sulfonic acid tetrahydro-pyran-4-ylmethyl ester as white crystalline solid. Yield: 99%, ES-MS: m/z 271 [M+H]; 1H NMR (400 MHz, CHLOROFORM-d) delta ppm1.19-1.35 (2H, m), 1.54-1.63 (2H, m), 1.85-2.02 (1H, m), 2.45 (3H, s), 3.28-3.39 (2H, m), 3.86 (2H, d, J=6.60 Hz), 3.93 (2H, dd, J=11.37, 4.52 Hz), 7.35 (2H, d, J=9.29 Hz), 7.78 (2H, d, J=8.31 Hz)

The synthetic route of 14774-37-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Boehringer Ingelheim International GmbH; US2010/76029; (2010); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1245724-46-2, (S)-Tetrahydro-2H-pyran-3-amine hydrochloride is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,1245724-46-2

A mixture of Int-15-3 (10 mg, 0.025 mmol), (S)-tetrahydro-2H-pyran-3- amine hydrochloride (7 mg, 0.051 mmol) and DIPEA (9 muL, 0.051 mmol) in 1,2- dichloroethane (0.2 mL) was stirred at RT for 10 min. To the mixture, NaBH(OAc)3 (11 mg, 0.051 mmol) and AcOH (3 muL, 0.051 mmol) were added. The resulting mixture was stirred RT overnight. The reaction mixture was concentrated under reduced pressure. The residue was purified by preparative-TLC (CH2Cl2:MeOH = 95:5) to give Compound 15 as yellow solid (10.2 mg, 84% yield). LCMS: (M+1) m/z = 480, 481

The synthetic route of 1245724-46-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; THE SCRIPPS RESEARCH INSTITUTE; BLACKTHORN THERAPEUTICS, INC.; ROBERTS, Edward; GUERRERO, Miguel A.; URBANO, Mariangela; ROSEN, Hugh; JONES, Rob; LAXAMANA, Candace Mae; ZHAO, Xianrui; TURTLE, Eric Douglas; (331 pag.)WO2018/170492; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics